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You'd better cleanup your iTunes library firstly. Just click "View > Show Duplicate Items" and then you would just check off the duplicates that you wanted to remove. After removed all the duplicates in your iTunes, sync it to your iPod, then all duplicates in your iPod will be removed automatically.
Source: http://how-to-delete-duplicates-in-itunes.newgenresoft.com/ How to Delete Duplicates in iTunes 12 11 10 9 automatically

If you do not already have iTunes you will need to go to www.apple.com/downloads
and download it there.
iTunes includes several options to automatically or manually sync videos to your iPod classic, iPod nano (3rd generation), or iPod (5th generation). Read this article to learn more about these two methods.
Products Affected
iTunes, iPod nano (3rd generation), iPod classic, iPod (5th generation)
Syncing videos automatically
Connect your iPod to your computer and open iTunes.
Select your iPod in the DEVICES section of the iTunes Source list.

In the main iTunes browser window, select the Music tab.
Select the checkbox labeled "Sync music" and verify that the "Include music videos" checkbox is also selected. You have the option to sync all songs and playlists or selected playlists.

Movies can be automatically synced to iPod. Select the Movies tab and select the option to sync all movies, selected movies, or a certain number recent unwatched movies.

TV Shows can be automatically synced to iPod. Select the TV Shows tab and select the option to sync all TV shows or selected ones. You can also determine which episodes are synced based on if they are recent or unwatched.

Video Podcasts can be automatically synced to iPod. Select the Podcasts tab select the option to sync all podcasts or selected ones. You can also determine which episodes are synced based on if they are recent, new or unplayed.

Click Apply and iTunes will begin syncing the content you've selected to your iPod. Tip: You can use the capacity bar at the bottom of the iPod settings window to determine how much free space is available. The size of a playlist can be determined by selecting it and looking at the bottom of the iTunes window.

The iTunes LCD will display the sync progress and notify you when the iPod sync is complete.

To disconnect your iPod, select it in the Source list and click the eject icon.
Syncing videos manually
If your prefer not to automatically sync video content to your iPod, you can setup manual syncing.
Connect your iPod to your computer and open iTunes.
Select your iPod in the DEVICES section of the iTunes Source list.

In the main iTunes browser window, select the Summary tab.
Select the "Manually manage music and videos" option. This will deselect the automatic sync settings for the Music, Movies, and TV Shows tabs. Automatic syncing for Podcasts, Photos, Contacts, and Games can be individually disabled by selecting each of those tabs. Note: When manually managing iPod, disk use is enabled and iPod must always be manually ejected in iTunes before disconnecting.

Click Apply.
To manually add music videos, movies or TV shows to your iPod, choose one of these categories under LIBRARY in the Source list.
Select and drag items you want (to choose multiple items, Command-click items on a Mac or Control-click items in Windows), then drag them onto your iPod icon in the Source list.
To add a playlist, select it in the Source list and drag it onto your iPod in the same ways as a video or song.

When you are ready disconnect your iPod, select it in the Source list and click the eject icon.

When you plug the iPod into the computer, iTunes should recognize the Nano after a minute or less. When it does, click on the icon of the Nano, and then click the Photos tab. Then check the box that says Sync from folder, and select the folder that your photos are stored in. The iTunes tool is not very precise or suer-friendly, and needs a lot of work. But, that is how it works. It usually only gives you an all-or-nothing choice - either load EVERY photo in a given folder, or load none of them. You may have to create a special folder on your desktop that you plan on storing only photos that you intend to sync to your iPod.

When you disconnect the iPod from your computer, you will be able to access your photos. You will also see that iTunes has created a "Photos" folder on your iPod where there wasn't one before.

Here are my directions: (I have the latest iTunes update)
1. Connect iPod to PC
2. Open iTunes
3. Click on icon of Nano
4. Click on Photos Tab
5. Deselect the box that says "Sync Photos from"
6. iTunes will then ask you if you no longer want to sync - tell it yes
7. iTunes will then ask you if you want to delete existing photos from your iPod - click on the box to delete all photos

Voila!

-Tha Mp3 Doctor

Here are Apple's Directions:
To delete photos from iPod nano:
1 Open iTunes, select iPod nano in the Source pane, and then click the Photos tab.
2 Select “Sync photos from:”
A On a Mac, choose iPhoto from the pop-up menu.
A On a Windows PC, choose Photoshop Album or Photoshop Elements from the
pop-up menu.
3 Choose “Selected albums” and deselect the albums or collections you no longer want
on iPod nano.
4 Click Apply.

Make sure you have the latest version of iTunes installed. Make sure iPod is not set to "Manual" mode. Click on the ipod icon under the devices menu in iTunes. You may have to scroll down to reveal the manual or sync settings in itunes window.

Use iTunes 8 to sync or delete songs, photos, etc.
Just connect the iPod to computer, download iTunes 8 from the internet, open iTunes 8, and then double-click on the icon of the iPod Nano to Sync files to your Nano.
The manual for the iPod Nano can be found at www.apple.com/support

Note: You cannot select a folder to which you do
not have write access, like a CD. Later versions of Adobe Photoshop
Album are not compatible. iTunes will only present the option to select
a folder if a later versions is installed.How much hard drive space do I need to sync my photos?
You need to have about as much free space on your hard drive as the
size of your collection of photos. iTunes constructs a photo database
on your hard drive in order to make photo syncing fast when you add new
photos in the future.What file formats can I sync to my iPod?
See iPod: Compatible photo formats for a list of file formats that can be used.Can I sync my photos to my iPod manually?
You can't drag individual photos or groups of photos to the iPod like
you can with music files in iTunes, but you can choose how you want
them to be synchronized (see below) by selecting the correct options:
iTunes 7 or later:

Connect your iPod to your computer.

Select the iPod icon when it appears in the iTunes window (below devices).

If you use iPhoto 4.0.3 or later in Mac OS X, you can
have iTunes automatically sync all of your photos and albums or just
certain albums every time you connect your iPod.

If
you are using Adobe Photoshop Elements versions 3.0 or later, you can
sync all of your photos or just certain collections of photos.

If
you are using Adobe Photoshop SE in Windows, you can sync either all of
your photos or certain collections of photos. If you are using Adobe
Photoshop Album SE in Windows, you can only sync all of your photos. Note: While Photoshop Album allows you to
sync only certain collections, Photoshop Album SE does not allow you to
assign collection tags that are required for this to work.

If
you are not using any of the above applications, you can sync all of
the photos in a selected folder, or only photos in specific folders
inside the selected folder. Folders inside the selected folder will be
displayed as photo albums on the iPod, but not subfolders beneath them.

Can I add photos from multiple computers or user accounts to one iPod?
No, adding photos can only happen from one computer or user account.Can I sync photos from my iPod to another computer?
No, all photo syncing is one way only, from computer to iPod. You can
put full-quality copies of all your photos on the iPod in the options
available in the Photos pane. Then drag the full-quality photos out of
the Photos folder on an iPod that has disk mode enabled to any other
computer.What does it mean when "Optimizing for iPod" appears in iTunes and what happens if I cancel?
iTunes creates TV-quality versions of your photos and stores them in a
database on your computer. This makes it much faster when you add new
photos to your iPod later. If you cancel this optimization, the photos
are not added to the iPod.